Alguns trabalhos futuros poderão ser realizados com a finalidade de melhorar os produtos monoméricos sintetizados:
- Purificação dos produtos monoméricos obtidos pelo método de abertura do anel epóxi, através, por exemplo, da técnica HPLC preparativo;
- Realizar, após a purificação, novas análises espectroscópicas de FTIR e de RMN 1H e 13C; - Formular novas composições dos compósitos dentários, variando a % m/m da parte orgânica;
- Realizar outro ensaios, como: contração de polimerização (contração volumétrica), sorção e solubilidade (avaliação da solubilidade em fluidos bucais) e resistência à flexão (determinação da máxima força que pode ser aplicada sem que o material tenha ruptura) e termogravimetria (estabilidade térmica); e,
- Investigar a substituição do GMA por outro composto que não leve a formação de isômeros pela abertura do anel.
REFERÊNCIAS
AGUIAR, T. R.; DI FRANCESCANTONIO, M.; BEDRAN-RUSSO, A. K.; GIANNINI, M. Inorganic Composition and Filler Particles Morphology of Convencional and Self Adhesive Resin Cements by SEM/EDX. Microsocpy Research and Technique, v. 75, n. 10, p. 1348- 1352, 2012.
ANUSAVICE, K. Resinas para restauração. In: Phillips materiais dentários. Rio de Janeiro: Guanabara Koogan, p. 161-177, 1998.
ANUSAVICE, K. Ciencia de los Materiales Dentales. 10 ed. Elsevier: Madrid; 2004.
ARIMA, T.; HAMADA, T.; McCABE, J. F. The effects of cross-linking agents on some properties of HEMA-based resins. Journal of Dental Research, v.74, n.9, p.1597, 1995.
ARIMA, T.; MURATA, H.; HAMADA, T. The effects of crosslinking agents on the water sorption and solubility characteristics of denture base resin. Journal of Oral Rehabilitation, v.23, n.7, p.476, 1996.
BACCHI, A.; SCHNEIDER, L. F.; MALAFAIA, F.; GARBOSSA, M. Resistência à flexão de resinas de metacrilato de metila e bisacrilato de metila submetidas à termociclagem. Revista de Odontologia UNESP, v.41, n.5, p.330-334, 2012.
BAQUEY, C.; MARMEY, P.; GUILLEMOT, F.; PORTÉ-DURRIEU, M-C. Des matériaux aux biomatériaux: Une conversion qui passe par des modes d’elaboration et de traitement de surface appropriés. Annales de Chimie Science des Matériaux, v.28, n.3, p.109-121, 2003. BILLMEYER JR., F. W. Ciencia de los polímeros. Editoral Reverté S.A. Barcelona, 1975. BLAUSEN GALLERY 2014. Wikiversity Journal of Medicine. Disponível em: https://en.wikiversity.org/wiki/Wikiversity_Journal_of_Medicine/Blausen_gallery_2014. Acessado em: 22/07/2015.
BOSMAN, A.; JANSSEN, H.; MEIJER, E. About dendrimers: structure, physical properties, and applications. Chemical Reviews, v.99, n.7, p.1665-1688, 1999.
BOULDEN, J.E.; CRAMER, N.B.; SCHRECK, K.M.; COUCH, C.L.; BRACHO- TROCONIS, C.; STANSBURY, J.W.; Thiol-ene-methacrylate composites as dental restorative materials. Dental Materials, v.27, p.267, 2011.
BOWEN, R. Dental filling material comprising vinyl-silane treated fused sílica and a binder consisting of the reaction product of bisphenol and glycidyl methacrylate. US Patent 3066112, 1962.
BOWEN, R. Properties of silica reinforced polymer for dental restorarion. Journal of the American Dental Association, v.66, p.57-64, 1963.
BRAGA, R.R.; FERRACANE, J.L. Contraction stress related to degree of conversion and reaction kinetics. Journal of Dental Research, v. 81, n. 2, p. 114-118, 2002.
CALHEIROS, F. C. Relação entre tensão de contração e grau de conversão em compósitos restauradores. Dissertação de Mestrado. Faculdade de Odontologia da Universidade de São Paulo. São Paulo, 2003.
CALLISTER JR., W. D. Materials Science and Engineering - An Introduction. Ed. 7, John Wiley & Sons, Inc. 2007.
CANEVALORO, S. V. Ciência dos Polímeros. 2ª Ed. Artliber, São Paulo, 2007.
CHAIN, M.; BARATIERI, L. Restaurações estéticas diretas em dentes posteriores. Ed. Artes Médicas. São Paulo; 2001.
CHEN, G.; KUMAR, J.; GREGORY, A.; STENZEL, M. H. Efficient synthesis of dendrimers via thiol-yne and esterification process and their potential application in the delivery of plainum anti-cancer drugs. Chemical Communications, v.41, p.6291-6293, 2009.
CHO, G. C.; KANEKO, L. M.; DONOVAN, T. E.; WHITE, S. N. Diametral and compressive strength of dental core materials. The Journal of Prosthetic Dentistry, v.82, n.3, p.272-276, 1999.
CLAYDEN, J.; GREEVES, N.; WARREN, S.; WOTHERS, P. Organic Chemistry. OUP Oxford, 1512 p., 2001.
COMBE, E. C.; BURKE, E. J. T.; DOUGLAS, W. H. Dental Biomaterials. Boston: Kluwer Academic Publisher, 1999.
CONCEIÇÃO, E. W. Restaurações Estéticas: compósitos, cerâmicas e implantes. Porto Alegre: Artmed, 2007.
CRAMER, N. B; COUCH, C.L.; SCHRECK, K.M.; CARIOSCIA, J.A.; BOULDEN, J.E.; STANSBURY, J. W.; BOWMAN, C. N. Investigation of thiol-ene and thiol-ene-methacrylate based resins as dental restorative materials. Dental Materials, v. 26, n.1, p. 21-28, 2010. CRAMER, N. B.; STANSBURY, J. W.; BOWMAN, C. N. Recent Advances and Developments in Composite Dental Restorative Materials. Journal of Dental Research, v. 90, n. 4, p. 402-416, 2011.
DA COSTA, R. T.; DELPECH, M. C.; COUTINHO, F. M. B. Estudo Viscosimétrico de Copolímeros em Blocos à Base de Poli (glicol propilênico) e Poli (glicol etilênico). 18º CBECiMat - Congresso Brasileiro de Engenharia e Ciência dos Materiais, p. 10116-10127, 2008.
DEGANI, A. L. G.; CASS, Q. B.; VIEIRA, P. C. Cromatografia: um breve ensaio. Química Nova na Escola, n.7, 1998.
DEMIR, M. M.; GULGUN, M. A.; MENCELOGLU, Y. Z. Metal Coated Nano Fibres. US Patent 20130082425 A1, 2013.
DePAOLI, M. A. Degradação e Estabilização de Polímeros. 2ª Ed., Chemkeys, 2008.
DeROUEN, T.; MARTIN, M.; LEROUX, B. TOWNES, B.; WOODS, J.; LEITÃO, J.; CASTRO-CALDAS, A.; LUIS, H.; BERNARDO, M.; ROSENBAUM, G.; MARTINS, I. Neurobehavioral Effects of Dental Amalgam in Children: A Randomized Clinical Trial. Journal of the American Medical Association, v.295, n.15, p.1784-1792, 2006.
DEWAELE, M.; LEPRINCE, J. G.; FALLAIS, I.; DEVAUX, J.; LELOUP, G. Benefits and Limitations of Assing Hyperbranched Polymers to Dental Resins. Journal of Dental Research, v.91, n.12, p.1178, 2012.
DOUDIUK-KENIG, H.; LIZENBOIM, K.; EPPELBAUM, I.; ZALSMAN, B.; KENIG, S. The effect of hyper-branched polymers on the properties of dental composites and adhesives. Journal of Adhesion Science and Technology, v.18, n.15, p.1723-1737, 2004.
DUCHEYNE, P.; KOHN, D. N. Materials for Bone and Joint Replacement. Materials Science and Technology-A Comprehensive Treatment, v. 14, p. 29-10, 1992.
DUREZA VICKERS. Disponível em: <http://dureza.weebly.com/uploads/1/8/7/8/18785222/ 3260625_orig.gif>. Acessado em: 03/12/2015.
EMAMI, N.; SÖDERHOLM, K. J. Young's Modulus and Degree of Conversion of Different Combination of Light-Cure Dental Resins. The Open Dentistry Journal, v.3, p.202-207, 2009. FARES, N. H.; NAGEM FILHO, H.; PACHECO, I. B.; COUTINHO, K. Q.; NAGEM, H. D. Resistência Flexural e Módulo de Elasticidade da Resina Composta. Revista de Clínica e Pesquisa Odontológica, v.2, n.1, p.53-55, 2005.
FERRACANE, J. L. Resin composite – State of the art. Dental Materials, v. 27, n. 1, p. 29-38, 2011.
FIALHO, E.; SILVA, E.; GRAFF, C.; LOGUERCIO, A.; CAMACHO, G.; BUSATO, A. Avaliação da infiltração marginal de restaurações de amálgama: mercúrio versus gálio. Pesquisa Odontológica Brasileira, v.14, n.1, p.59-63, 2000.
FINER, Y.; SANTERRE, J. P. The influence of resin chemistry on a dental composite’s biodegradation. Journal of Biomedical Materials Research, part A, v.69(A), p.233, 2004. FLORY, P. J. Molecular Size Distribution in Three Dimensional Polymers. VI. Branched Polymers Containing A-R-B,-, Type Units. Journal of the American Chemical Society, v.74, n.11, p.2718, 1952.
FONSECA, M. G.; AIROLDI. C. Híbridos inorgânico-orgânicos derivados da reação de filossilicatos com organossilanos. Química Nova, v. 26, n. 5, p. 699-707, 2003.
GALINA, H.; LECHOWICZ, J. B.; WALCZAK, M. Model of Hyperbranched Polymerization Involving AB2Monomer and B3 Core Molecules both Reacting with Substitution Effect. Macromolecules, v.35, n.8, p.3261, 2002.
GAUTHIER, M. A.; ZHANG, Z.; ZHU X. X. New dental composites containing multimethacrylate derivatives of bile acids: a comparative study with commercial monomers. ACS Applied Materials & Interfaces. v. 1, n. 4, p. 824-832, 2009.
GAO, C.; YAN, D. Hyperbranched polymers: from synthesis to applications. Progress in Polymer Science. 29: 183, 2004.
GENTLEMAN, E.; BALL, M. D.; STEVENS, M. M.; Biomaterials. Medical Sciences, v. 2., 2010. Disponível em: <http://www.eolss.net/sample-chapters/c03/E6-59-13-07.pdf>. Acessado em: 09/03/2015.
GUASTALDI, A.C.; APARECIDA, A.H. Fosfatos de cálcio de interesse biológico: importância como biomateriais, propriedades e métodos de obtenção de recobrimentos. Química Nova, v. 33, n. 6, p. 1352-1358, 2010.
HA, J.Y.; KIM S.H., KIM K.H., KWON T.Y. Influence of the volumes of bis-acryl and poly (methyl methacrylate) resins on their exothermic behavior during polymerization. Dental Materials Journal, v. 30, n. 3, p. 336-342, 2011.
HAGIO, M.; KAWAGUCHI, M.; MOTOKAWA, W.; MIYAZAKI, K. Degradation of methacrylate monomers in human saliva. Dental Materials, v.25, n.2, p.241, 2006.
HOLLER, F. J.; SKOOG. D. A.; CROUCH S. R. Príncipios de Análise Instrumental. 6. ed. Porto Alegre: Bookman, 2009.
HOYLE, C. E.; LEE, T. Y.; ROPER, T. Thiol-Ene Click Chemistry. Angewandte Chemie International Edition, v.49, p.1540-1573, 2010.
HUGGINS, M. L. The Viscosity of Dilute Solutions of Long-Chain Molecules. IV. Dependence on Concentration. Journal of American Chemical Society, v.64, n.11, p.2716-2718, 1942. IONASHIRO, M.A.; GIOLITO, I. Nomenclatura, padrões e apresentação dos resultados em análise térmica. Cerâmica, São Paulo, v.26, n.121, p.17-24, 1980.
JUNIOR, P. C. M.; CARDOSO, R. M.; MAGALHAES, B. G.; GUIMARAES, R. P.; SILVA, C. H. V.; BEATRICE, L. C. S. Selecionando Corretamente as Resinas Compostas. Internacional Journal of Dentistry, Recife, v.10, n.2, p.91-96, 2011.
KARABELA, M. M.; SIDERIDOU. I. D. Synthesis and study of properties of dental resin composites with different nanosilica particles size. Dental Materials, v. 27, n. 8, p. 825-835, 2011.
KAWACHI, E. Y.; BERTRAN, C. A.; DOS REIS, R. R.; ALVES, O. L. Biocerâmicas: tendências e perspectivas de uma área interdisciplinar. Química Nova, v.23, n.4, 2000. KAWAGUCHI, T.; LASSILA, L. V. J.; VALLITTU, P. K.; TAKAHASHI, Y. Mechanical properties of denture base resin cross-linked with methacrylated dendrimer. Dental Materials, v. 27, n. 8, p. 755 -761, 2011.
KENSHIMA, S.; FRANCCI, C.; REIS, A.; LOGUERCIO, A. D.; FILHO, L. E. Conditioning effect on dentin, resin tags and hybrid layer of different acidity self-etch adhesives applied to thick and thin smear layer. Journal of Dentistry, v. 34, n. 10, p. 775-783, 2006.
KHATRI, C. A.; STANSBURY, J. W.; SCHULTHEISZ, C. R.; ANTONUCCI, J. M. Synthesis, characterization and evaluation of urethane derivatives of Bis-GMA. Dental Materials, v. 19, n. 7, p. 584-588, 2003.
KILLOPS, K.; CAMPOS, L.; HAWKER, C. Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene “click” chemistry. Journal of the American Chemical Society, v.130, p.5062-5064, 2008.
KRAEMER, E. O. Molecular Weights of Celluloses and Cellulose Derivates. Industrial & Engineering Chemistry, v.30, n.10, p.1200-1203, 1938.
KRIEGER, S. Biocerâmica. Universidade de São Paulo, 2003.
KRYGER, M. Applications of thiol-ene coupling. Organic Chemistry Seminar Abstract. The Department of Chemistry at the University of Illinois, 2008/2009.
KUSGOZ, A.; TUZUNER, T.; ULKER, M.; KEMER, B.; SARAY, O. Conversion degree, microhardness, microleakage and fluoride release of different fissure sealants. Journal of the Mechanical Behavior of Biomedical Materials, v.3, n.8, p.594-599, 2010.
LEE, T.; CARIOSCIA, J.; SMITH, Z.; BOWMAN, C. Thiol-allyl ether-methacrylate ternary systems. Evolution mechanism of polymerization-induced shrinkage stress and mechanical properties. Macromolecules, v.40, p.1473-1479, 2007.
LU, H.; CARIOSCIA, J.; STANSBURY, J.; BOWMAN, C. Investigations of step-growth thiol-ene polymerizations for novel dental restoratives. Dental Material, v.21, p.1129-1136, 2005.
LUZYANIN, K.; ABRANTES. M. Ressonância Magnética Nuclear – Ferramenta Versátil em Química Farmacêutica e Imagiologia Médica. Sociedade Portuguesa de Química, v.117, p.25-30, 2010.
MANSOUR, S.H.; MOSTAFA, N.; ABD-EL-MESSIEH L. Electrical and positron annihilation study on epoxy and epoxy acrylate composites. European Polymer Journal, v. 43, n. 11, p. 4770-4782, 2007.
MARCOS, M.; SERRANO, J. L. Polímeros Dendríticos. Anales de Química, v.105, n.2, p.103, 2009.
MARSHALL, S. J.; BALOOCH, M.; BREUNIG, T.; KINNEY, J. H.; TOMSIA, A. P.; INAI, N.; WATANABE, L. G.; WU-MAGIDI, I. C.; MARSHALL JR, G. W. Human dentin and the dentin-resin adhesive interface. Acta Mater., v. 46, n. 7, p. 2529-2539, 1998.
MARTIN, N; JEDYNAKIEWICZ, N. Measurement of water sorption in dental composites. Biomaterials, v. 19, p. 77-83, 1998.
MATINLINNA, J. P.; LASSILA, L. V. J.; OZCAN, M.; YLI-URPO, A.; VALLITTU, P. K. An Introduction to silanes and their clinical applications in Dentistry. The International Journal of Prosthodontics, v. 17, n. 2, p. 155-164, 2004.
MATINLINNA, J. P.; LASSILA, L. V. J.; KANGASNIEMI, I.; YLI-URPO, A.; VALLITTU, P. K. Shear bond strength of Bis-GMA resin and methacrylated dendrimer resins on silanized titanium substrate. Dental Materials, v. 21, p. 287-296, 2005.
MATTHEWS, F. L.; RAWLING, R. D. Composite Materials: Engineering and Science. Woodhead Publishing Limited, 1ª Ed., 1994.
MENDES, L.C.; TEDESCO, A. D.; MIRANDA, M.S.; BENZI, M.R.; CHAGAS, B.S. Determination of degree of conversion as a function of depth of a photo-initiated dental
restoration composite-II application to commercial SureFilTM. Polymer Testing, v. 24, n. 7, p. 942-946, 2005.
MILETIC, V. Water sorption and solubility of resin-based composites. Disponível em <http://dental-materials.blogspot.com.br/2011/02/water-sorption-and-solubility-of-
resin.html>. Acessado em 29/07/2015.
MIRSASAANI, S. S.; ATAI. M. M.; HASANI-SADRABADI M. M. Photopolymerization of a dental nanocomposite as restorative material using the argon laser. Lasers in Medical Science, v. 26, n. 5 p. 553-561, 2011.
MOSZNER, N.; SALZ, U. New Developments of Polymeric Dental Composites. Progress in Polymer Science, v.26, p.535, 2001.
MOTTA, R. G. Aplicações Clínicas dos Materiais Dentários. Editora de Publicações Científicas. Rio de Janeiro, c.1-6, p.1-41, 1991.
MOUSAVINASAB, S. M. Biocompatibility of composite resins. Dental Research Journal, v.8, n.1, p.S21, 2011.
NICOLAE, L. C.; SHELTON, R. M.; COOPER, P. R.; MARTIN, R. A.; PALIN, W. M. The Effect of UDMA/TEGDMA Mixtures and Bioglass Incorporation on the Mechanical and Physical Properties of Resin and Resin-Based Composite Materials. Conference Papers in Science, vol. 2014, Article ID 646143, 5 pages, 2014.
PARK, J. G.; YE, Q.; TOPP, E. M.; SPENCER, P. Enzymecatalysed hydrolysis of dentin adhesives containing a new urethane based trimethacrylate monomer. Journal of Biomedical Materials Research: Part B – Applied Biomaterials, v. 91, n. 2, p. 562-571, 2009.
PARK, J; ESLICK, J.; YE, Q.; MISRA, A.; SPENCER, P. The influence of chemical structure on the properties in methacrylate-based dentin adhesives. Dental Materials, v. 27, n. 11, p. 1086-1093, 2011.
PAVLINEC, J.; ZEUNER, F.; ANGERMANN, J.; MOSZNER, N. Synthesis and radical polymerization behaviour of 2,4,6-trimethylphenyl-2-[4-(dihydroxyphosphory)-2-oxabutyl] acrylate. Macromolecular Chemistry and Physics, v. 206, n. 18, p. 1878-1886, 2005.
PELKA, M.; DANZL, C.; DISTLER, W.; PETSCHELT, A. A new screening test for toxicity testing of dental materials. Journal of Dentistry, v.28, n,5, p.341, 2000.
PEUTZFELDT, A.; Resin composites in dentistry: the monomer systems. European Journal of Oral Sciences, v. 105, n. 2, p. 97-116, 1997.
PEUTZFELDT, A.; ASMUSSEN, E. The effect os postcuring on quantity of remaining double bonds, mechanical properties, and in vitro wear of two resins composites. Journal of Dentistry, v. 28, n. 6, p. 447-452, 2000.
PFEIFFER, P.; ROSENBAUER, E. U. Residual methyl methacrylate monomer, water sorption and water solubility of hypoallergenic denture base materials. Journal of Prosthetic Dentistry, v.92, n.1, p.72, 2004.
PHILLIPS, R. Materiais dentários de Skinner. 8ª ed. Rio de Janeiro: Guanabara; 1986.
PODGORSKI, M. Synthesis and characterization of novel dimethacrylates of different chain lengths as possible dental resins. Dental Materials, v.26, n.6, p.188–194, 2010.
POSKUS, L. T.; PLACIDO, E.; CARDOSO, P. E. C. Influence of placement techniques on Vickers and Knoop hardness of class II composite resin restorations. Dental Materials, v.20, n.8, p.726-732, 2004.
POSNER, T. Beiträge zur Kenntniss der ungesättigten Verbindungen. II. Ueber die Addition von Mercaptanen an ungesättigte Kohlenwasserstoffe. Berichte der deutschen chemischen Gesellschaft, v. 38, n. 1, p. 646–657, 1905.
PRASAD, A.; SARKAR, N. Restorative Composite Resins. In: Contemporary dental materials. ed. V. Dhuru B. Oxford University Press. Oxford; 2004.
QUINCY, A. S. Synthesis and Characterization of Functional Polymers with Controlled Architecture and Their Application as Anticorrosion Primers. Ed. ProQuest. University of New Hamsphire, 2009.
RAHMAN, I. A.; PADAVETTAN, V. Sythesis of Silica Nanoparticles by Sol-Gel: Size- Dependent Properties, Surface Modification, and Application in Silica-Polymer Nanocomposites-Review. Journal od Nanomaterials, v. 2012, n. 8, p. 1-15, 2012.
RAMAKHARISNA, S.; MAYER, J.; WINTERMANTEL, E.; LEONG, K. W. Biomedical applications of polymer-composite materials: a review. Composites Science and Technology, v.61, p.1189-1224, 2001.
RAO, P.; AASEN, S.; ERDOGAN-HAUG, B.; GADDAM, B.; ROIKO, R.; JOSEPH, E. Dental filling composition comprising hyperbranched compound. US Patent 20110045444 A1, 2011.
RASTELLI, A. N. S.; JACOMASSI D. P.; FALONI, A. P. S.; QUEIROZ, T. P.; ROJAS, S. S.; BERNARDI, M. I. E.; BAGNATO, V. S.; HERNANDES, A. C. The Filler Content of the
Dental Composite Resins and Their Influence on Different Properties. Microscopy research and technique, v. 75, n. 6, p. 758-765, 2012.
REIS, A.; LOGUERCIO, A. D. Materiais Dentários Restauradores Diretos: dos Fundamentos à Aplicação Clínica. 1ª ed., São Paulo: Santos, 2007.
REIS, A. V.; FAJARDO, A. R.; SCHUQUEL, I. T. A.; GUILHERME, M. R.; VIDOTTI, G. J.; RUBIRA, A. F.; MUNIZ, E. C. Reaction of Glycidyl Methacrylate at the Hydroxyl and Carboxylic Groups of Poly(vinyl alcohol) and Poly(acrylic acid): Is This Reaction
Mechanism Still Unclear? Journal Organic Chemistry, v. 74, n. 10, p. 3750-3757, 2009.
RODRIGUES, G. D. R.; PEREIRA, S. N. A. Evolución y tendencias actuales en resinas compuestas. Acta Odontológica Venezoelana, v. 46, n. 3, p. 1-19, 2008.
ROSS, M. H.; KAYNE, G. I.; PAWLINA, W. Histology: a Text and Atlas. Ed. 4, 875 p., Baltimore: Lippincott Williams & Wilkins, 2002.
RUEGGEBERG, F. Contemporary issues in photocuring. Compendium of Continuing Education in Dentistry (Supplement), v. 25, p. 4-15, 1999.
SALERNITANO, E.; MIGLIARESI, C. Composite materials for biomedical applications: a review. Journal of Applied Biomaterials & Biomechanics, v. 1, p. 3-18, 2003.
SALGADO, N. R. G. F.; BOARO, L. C. C.; ORNAGHI, B. P.; PFEIFER, C. S.; FRANCCI, C. E.; MEIER, M. M.; BRAGA, R. R. Influence of the Base and diluent methacrylate monomers on the polymerization stress and its determinants. Journal of Applied Polymer Science, v.123, n.5, p.2985-2991, 2012.
SANDNER, B.; BAUDACH, S.; DAVY, K. W. M.; BRADEN M.; CLARKE, R. L. Synthesis of Bis-GMA derivatives, properties of their polymers and composites. Journal of Materials Science: Materials in Medicine, v. 8, n. 1, p. 39-44, 1997.
SCHOTT. Operating Instructions - Cannon-Fenske Routine Viscosimeter.
SHALABY, S. W.; SALZ, U. Polymers for dental and orthopedic applications. CRC Press - Taylor & Francis Group, 2007.
SIDERIDOU, I.; TSERKI, V.; PAPANASTASIOU, G. Effect of chemical structure on degree of conversion in light-cured dimethacrylate-based dental resin. Biomaterials, v.23, n.8, p.1819, 2002.
SEDERIDOU, I.; TSERKI, V.; PAPANASTASIOU, G. Study of water sorption, solubility and modulus of elasticity of light-cured dimethacrylate-based dental resins. Biomaterials, n.24, v.4, p.655-665, 2003.
SIDERIDOU, I.; ACHILIAS, D. S.; KYRIKOU, E. Thermal expansion characteristics of light-cureddental resins and resin composites. Biomaterials, v.25, p.3087-3097, 2004.
SIGMA-ALDRICH®. Disponível em: <www.sigmaaldrich.com>, 2015.
SILVA, A. L. B. B.; DA SILVA, E. O. Conhecendo Materiais Poliméricos. Grupo de Pesquisa em Novos Materiais. Universidade Federal de Mato Grosso (UFMT), 2003.
SILVERSTEIN, R. M.; WEBSTER, F. X.; KIELME, D. J. Spectrometric Identification of Organic Compounds. John Wiley & Sons, Inc., 7th Ed., United States of America, 2005. SOCRATES, G. Infrared and Raman Characteristic Group Frequencies, Tables and Charts. John Wiley & Sons Ltd., 3rd Ed., England, 347 p., 2001.
STANSBURY, J. W. Cyclopolymerizable monomers for use in dental resin composites. Journal of Dental Research, v. 69, n. 3, p. 844-848, 1990.
STANSBURY, J. W. Synthesis and evaluation of novel multifunctional oligomers for dentistry. Journal of Dental Research, v. 71, n. 3, p. 434-437, 1992.
TAKAHASHIA, Y.; TSURUTA, S.; HASEGAWA, J.; KAMEYAMAB, Y.; YOSHIDA, M. Release of mercury from dental amalgam fillings in pregnant rats and distribution of mercury in maternal and fetal tissues. Toxicology, v.163, p.115-126, 2001.
TEN CATE, A.R. Oral Histology: development, structure, and function. Ed. 5, 497 p., St. Louis: Mosby, 1998.
TESHIMA, W.; NOMURA, Y.; IKEDA, A.; KAWAHARA, T.; OKAZAKI, M.; NAHARA, Y. Thermal degradation of photo-polymerized bisGMA/TEGDMA based dental resins. Polymer Degradation and Stability, v. 84, n. 1, p. 167-172, 2004.
THERMO NICOLET CORPORATION. Introduction to Fourier Transform Infrared Spectrometry, 2001. Disponível em: <http://mmrc.caltech.edu/FTIR/FTIRintro>. Acesso em: 10/07/2015.
TOMASIK, A.; BIERNAT, M.; PARZUCHOWSKI, P. Hyperbranched multimethacrylate resins of low viscosity and low oxygen inhibition for dental applications. Polimery, v.55, n.4, p.284-292, 2010.
TRUFFIER-BOUTRY, D.; PLACE, E.; DEVAUX, J.; LELOUP, G. Interfacial layer characterization in dental composite. Journal of Oral Rehabilitation. v.30, p 74-77, 2003.
VIMMY, M.; TAKAHASH, Y.; LORSCHEIDER, F. Material-fetal distributionof mercury (203Hg) released from dental amalgam filing. American Journal of Physiology, v.258, n.4, p.939-945, 1990.
XIONG, J.; SUN, X.; CHEN, J.; TANG, L. Influence of Filler Content on Physicomechanical and Bonding Properties of an Experimental Dental Resin Cement. Journal of Applied Polymer Science, v. 127, n. 4, p. 2427-2434, 2013.
WAN, Q; SCHRICKER, S. R.; CULBERTSON, B. M. Methacryloyl derivitized hyperbranched polyester. 2. Photo-polymerization and properties for dental resin systems. Journal of Macromolecular Science. A37, v.11, n.11, p.1317-1331, 2007.
WANG, R.; ZHU, MO; BAO, S.; LIU, F.; JIANG, X.; ZHU, MEIFANG. Synthesis of Two Bis-GMA Derivates with Different Size Substituents as Potential Monomer to Reduce the Polymerization Shrinkage of Dental Restorative Composites. Journal of Materials Science Research, v. 2, n. 4, p. 12-22, 2013.
WILLIAMS, D. F.; CUNNINGHAM, J. Materials in Clinical Dentistry. Oxford, UK: Oxford University Press, 1979.
WSFA. Biomaterials Market Growth Forecast at 16% CAGR to 2020. Disponível em: < http://www.wsfa.com/story/30736668/biomaterials-market-growth-forecast-at-16-cagr-to- 2020>. Acessado em: 17/12/15.
YAP, A. U. J; WANG, X.; WU, X.; CHUNG, S. W. Comparative hardness and modulus of tooth-colored restoratives: A depth-sensing microindentation study. Biomaterials, v. 25, n. 11, p. 2179-2185, 2004.
YEA, S.; AZARNOUSHB, S.; SMITHA, I. R.; CRAMERA, N. B.; STANSBURYC, J. W.; BOWMANA, C. N. Using hyperbranched oligomer functionalized glass fillers to reduce shrinkage stress. Dental Materials, v.28, n.9, p.1004-1011, 2012.
YOSHIDA, Y.; NAGAKANE, K.; FUKUDA, R.; NAKAYAMA, Y.; OKAZAKI, M.; SHINTANI, H. Comparative study on adhesive performance of functional monomers. Journal of Dental Research, v. 83, n. 6, p. 454-458, 2004.
YOO, S. H.; PARK, K.; KIM, J.; KIM, C. K. Characteristics of Dental Restorative Composites Fabricated from BisGMA Alternatives and Spiro Orthocarbonates. Macromolecular Research, v.19, n.1, p.27-32, 2011.
ZHAO, J. & XIE, D. A novel hyperbranched poly(acrylic acid) for improved resin-modified glass-ionomer restoratives. Dental Materials, v.27, n.5, p.478-486, 2011.